Organometallic compound, composition containing organometallic compound, and organic light-emitting device including the same

ABSTRACT

An organometallic compound represented by Formula 1: 
                         
wherein in Formula 1, R 11  to R 20 , L 11 , m 11 , and n 11  are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0018137, filed on Feb. 5, 2015, in the KoreanIntellectual Property Office, the disclosure of which is incorporatedherein in its entirety by reference.

BACKGROUND

1. Field

The present disclosure relates to an organometallic compound, acomposition containing an organometallic compound, and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs exhibit excellent luminance, drivingvoltage, and response speed characteristics, and produce full-colorimages.

A typical organic light-emitting device includes an anode, a cathode,and an organic layer that is disposed between the anode and the cathodeand includes an emission layer. A hole transport region may be disposedbetween the anode and the emission layer, and an electron transportregion may be disposed between the emission layer and the cathode. Holesprovided from the anode may move toward the emission layer through thehole transport region, and electrons provided from the cathode may movetoward the emission layer through the electron transport region. Theholes and the electrons are recombined in the emission layer to produceexcitons. These excitons change from an excited state to a ground stateto thereby generate light.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Provided are an organometallic cyclic compound and an organiclight-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented exemplary embodiments.

According to an aspect of an exemplary embodiment, an organometalliccompound is represented by Formula 1:

wherein in Formula 1,

R₁₁, R₁₂, and R₁₄ to R₁₈ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a carbonyl group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₂-C₁₀ alkynyl group, and a substituted orunsubstituted C₁-C₁₀ alkoxy group;

R₁₃ is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a carbonyl group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₁₀ linear alkyl group, a substituted or unsubstitutedC₂-C₁₀ alkenyl group, a substituted or unsubstituted C₂-C₁₀ alkynylgroup, and a substituted or unsubstituted C₁-C₁₀ alkoxy group;

R₁₉ and R₂₀ are each independently selected from a hydrogen, adeuterium, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkyl group substitutedwith a deuterium;

at least one of R₁₁ to R₂₀ is a deuterium-containing substituent;

n11 is selected from 1, 2, and 3;

L₁₁ is selected from a monodentate ligand and a bidentate ligand; and

m11 is selected from 0, 1, 2, 3, and 4.

According to one or more exemplary embodiments, a composition containingan organometallic compound, includes:

a first organometallic compound represented by Formula 1 and

a second organometallic compound represented by Formula 2:

wherein in Formulae 1 and 2,

R₁₁, R₁₂, and R₁₄ to R₁₈ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a carbonyl group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₂-C₁₀ alkynyl group, and a substituted orunsubstituted C₁-C₁₀ alkoxy group;

R₁₃ is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a carbonyl group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₁₀ linear alkyl group, a substituted or unsubstitutedC₂-C₁₀ alkenyl group, a substituted or unsubstituted C₂-C₁₀ alkynylgroup, and a substituted or unsubstituted C₁-C₁₀ alkoxy group;

R₁₉ and R₂₀ are each independently selected from a hydrogen, adeuterium, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkyl group substitutedwith a deuterium;

at least one of R₁₁ to R₂₀ is a deuterium-containing substituent;

R₂₁, R₂₂, and R₂₄ to R₂₈ are each independently selected from ahydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a carbonyl group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₁₀ alkyl group, asubstituted or unsubstituted C₂-C₁₀ alkenyl group, a substituted orunsubstituted C₂-C₁₀ alkynyl group, and a substituted or unsubstitutedC₁-C₁₀ alkoxy group;

R₂₃ is selected from a hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a carbonyl group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀linear alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group,a substituted or unsubstituted C₂-C₁₀ alkynyl group, and a substitutedor unsubstituted C₁-C₁₀ alkoxy group;

R₂₉ and R₃₀ are each independently selected from a hydrogen and a C₁-C₁₀alkyl group;

R₂₁ to R₃₀ are each a substituent comprising no deuterium;

n11 and n21 are each independently selected from 1, 2, and 3;

L₁₁ and L₂₁ are each independently selected from a monodentate ligandand a bidentate ligand; and

m11 and m21 are each independently selected from 0, 1, 2, 3, and 4.

According to an aspect of another exemplary embodiment, an organiclight-emitting device includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and at least oneorganometallic compound represented by Formula 1.

The emission layer may include the organometallic compound, the emissionlayer may further include a host, and the organometallic compoundincluded in the emission layer may serve as a dopant.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the exemplary embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic cross-sectional view illustrating an organiclight-emitting device according to an embodiment;

FIG. 2A is a graph of weight (%) versus temperature (degree Centigrade,° C.), which shows a result of Thermo Gravimetric Analysis (TGA) onCompound 6 according to an embodiment;

FIG. 2B is a graph of weight (%) and weight changes (percent per degreeCentigrade, %/° C.) versus temperature (degree Centigrade, ° C.), whichshows a result of TGA on Compound 7 according to an embodiment;

FIG. 3A is a graph of intensity (arbitrary units, a. u.) versuswavelength (nanometers, nm) showing a photoluminescence (PL) spectrumand an ultraviolet (UV) absorption spectrum of Compound 6 according toan embodiment;

FIG. 3B is a graph of intensity (arbitrary units, a. u.) versuswavelength (nanometers, nm) showing a PL spectrum and a UV absorptionspectrum of Compound 7 according to an embodiment;

FIG. 4 is a graph of current density (milliamperes per squarecentimeter, mA/cm²) illustrating current density changes according tovoltages of organic light-emitting devices manufactured in Example 1 andComparative Example 1;

FIG. 5 is a graph of intensity (arbitrary units, a. u.) versuswavelength (nanometers, nm) showing electroluminescence (EL) spectrum ofthe organic light-emitting devices manufactured in Example 1 andComparative Example 1;

FIG. 6 is a graph of efficiency (arbitrary units, a. u.) versusluminance (candelas per square meter, cd/m²) illustrating conversionefficiency changes according to luminance values of the organiclight-emitting devices manufactured in Example 1 and Comparative Example1; and

FIG. 7 is a graph of luminance (percent) versus time (hours, hrs)illustrating lifespan of the organic light-emitting devices manufacturedin Example 1 and Comparative Example 1.

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examplesof which are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present exemplary embodiments may have different forms and shouldnot be construed as being limited to the descriptions set forth herein.Accordingly, the exemplary embodiments are merely described below, byreferring to the figures, to explain aspects. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “comprises” and/or“comprising,” or “includes” and/or “including” when used in thisspecification, specify the presence of stated features, regions,integers, steps, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,regions, integers, steps, operations, elements, components, and/orgroups thereof.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the exemplary term “below” can encompass both anorientation of above and below. The device may be otherwise oriented(rotated 90 degrees or at other orientations) and the spatially relativedescriptors used herein interpreted accordingly.

About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this invention belongs. It will befurther understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the relevant art and thepresent disclosure, and will not be interpreted in an idealized oroverly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

An organometallic compound is represented by Formula 1:

wherein in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, a carbonyl group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group,a substituted or unsubstituted C₂-C₁₀ alkynyl group, and a substitutedor unsubstituted C₁-C₁₀ alkoxy group.

In some embodiments, in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, and a substituted or unsubstituted C₁-C₁₀alkyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, and a C₁-C₁₀alkyl group; and a C₁-C₁₀ alkyl group substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, and a cyano group, butembodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, and a C₁-C₁₀alkyl group; and a C₁-C₁₀ alkyl group substituted with a deuterium, butembodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, anda tert-pentyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, anda tert-pentyl group, each substituted with a deuterium, but embodimentsare not limited thereto.

In some embodiments, in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₅ may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₁, R₁₅, and R₁₇ may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₁ or R₁₅ may be each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group,a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₁ and R₁₅ may be each independentlyselected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a carbonyl group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₁₀ linear alkyl group, asubstituted or unsubstituted C₂-C₁₀ alkenyl group, a substituted orunsubstituted C₂-C₁₀ alkynyl group, and a substituted or unsubstitutedC₁-C₁₀ alkoxy group.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a carbonyl group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, and a substituted or unsubstituted C₁-C₁₀ linear alkyl group,but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₁₀ linear alkylgroup; and

a C₁-C₁₀ linear alkyl group substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, and a cyano group, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, and a C₁-C₁₀ linear alkylgroup; and

a C₁-C₁₀ linear alkyl group substituted with a deuterium, butembodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an n-butyl group, and an n-pentyl group; and

a methyl group, an ethyl group, an n-propyl group, an n-butyl group, andan n-pentyl group, each substituted with a deuterium, but embodimentsare not limited thereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, and an n-butyl group; and

a methyl group an ethyl group, an n-propyl group, and an n-butyl group,each substituted with a deuterium, but embodiments are not limitedthereto.

In some embodiments, in Formula 1, R₁₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, and anethyl group; and

a methyl group and an ethyl group, each substituted with a deuterium,but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₁ and R₁₂, R₁₂ and R₁₃, R₁₃ andR₁₄, or R₁₄ and R₁₅ may be optionally linked to each other to form acondensed ring, but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₅ and R₁₆ may be optionally linkedto each other via a single bond, but embodiments are not limitedthereto.

In some embodiments, in Formula 1, R₁₉ and R₂₀ may be each independentlyselected from a hydrogen, a deuterium, a C₁-C₁₀ alkyl group, and aC₁-C₁₀ alkyl group substituted with a deuterium.

In some embodiments, in Formula 1, R₁₉ and R₂₀ may be each independentlyselected from

a hydrogen;

a deuterium;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, R₁₉ and R₂₀ may be each independentlyselected from a hydrogen and a deuterium, but embodiments are notlimited thereto.

In some embodiments, in Formula 1, R₁₉ may be a deuterium, and R₂₀ maybe a hydrogen, but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₉ may be a hydrogen, and R₂₀ may bea deuterium, but embodiments are not limited thereto.

In some embodiments, in Formula 1, R₁₉ and R₂₀ may both be a deuterium,but embodiments are not limited thereto.

In Formula 1, at least one of R₁₁ to R₂₀ may be a deuterium-containingsubstituent.

In some embodiments, in Formula 1, at least one of R₁₁, R₁₂, and R₁₄ toR₁₈ may be a deuterium-containing substituent, but embodiments are notlimited thereto.

In some embodiments, in Formula 1, at least one of R₁₁, R₁₅, and R₁₇ maybe a deuterium-containing substituent, but embodiments are not limitedthereto.

In some embodiments, in Formula 1, R₁₁ or R₁₅ may be adeuterium-containing substituent, but embodiments are not limitedthereto.

In some embodiments, in Formula 1, R₁₁ and R₁₅ may be each independentlya deuterium-containing substituent, but embodiments are not limitedthereto.

In some embodiments, in Formula 1, R₁₁, R₁₅, and R₁₇ may be eachindependently a deuterium-containing substituent, but embodiments arenot limited thereto.

In the present specification, the term “deuterium-containingsubstituent” refers to a deuterium or a substituent that contains atleast one deuterium. For example, a deuterium-containing substituent mayrefer to a substituent that is obtained by substituting at least onehydrogen atom in a substituent such as a C₁-C₃₀ alkyl group, a C₆-C₃₀aryl group, or the like as described above with a deuterium atom.

In some embodiments, in Formula 1, the deuterium-containing substituentmay be selected from

a deuterium; and

a C₁-C₁₀ alkyl group substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, the deuterium-containing substituentmay be selected from

a deuterium; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, anda tert-pentyl group, each substituted with a deuterium, but embodimentsare not limited thereto.

In some embodiments, in Formula 1, the deuterium-containing substituentmay be selected from

a deuterium; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, each substituted with a deuterium, but embodiments arenot limited thereto.

In some embodiments, in Formula 1, the deuterium-containing substituentmay be selected from

-D, —CH₂D, —CHD₂, —CD₃, —CH₂CH₂D, —CH₂CHD₂, —CH₂CD₃, —CHDCH₃, —CHDCH₂D,—CHDCHD₂, —CHDCD₃, —CD₂CH₃, —CD₂CH₂D, —CD₂CHD₂, —CD₂CD₃, —CH₂CH₂CH₂D,—CH₂CH₂CHD₂, —CH₂CH₂CD₃, —CH₂CHDCH₃, —CH₂CHDCH₂D, —CH₂CHDCHD₂,—CH₂CHDCD₃, —CH₂CD₂CH₃, —CH₂CD₂CH₂D, —CH₂CD₂CHD₂, —CH₂CD₂CD₃,—CHDCH₂CH₂D, —CHDCH₂CHD₂, —CHDCH₂CD₃, —CHDCHDCH₃, —CHDCHDCH₂D,—CHDCHDCHD₂, —CHDCHDCD₃, —CHDCD₂CH₃, —CHDCD₂CH₂D, —CHDCD₂CHD₂,—CHDCD₂CD₃, —CD₂CH₂CH₂D, —CD₂CH₂CHD₂, —CD₂CH₂CD₃, —CD₂CHDCH₃,—CD₂CHDCH₂D, —CD₂CHDCHD₂, —CD₂CHDCD₃, —CD₂CD₂CH₃, —CD₂CD₂CH₂D,—CD₂CD₂CHD₂, —CD₂CD₂CD₃, —CH(CH₃)(CH₂D), —CH(CH₃)(CHD₂),—CH(CH₂D)(CH₂D), —CH(CH₃)(CD₃), —CH(CHD₂)(CHD₂), —CH(CH₂D)(CD₃),—CH(CHD₂)(CHD₂), —CH(CHD₂)(CD₃), —CH(CD₃)₂, —CD(CH₃)₂, —CD(CH₃)(CH₂D),—CD(CH₃)(CHD₂), —CD(CH₂D)(CH₂D), —CD(CH₃)(CD₃), —CD(CHD₂)(CHD₂),—CD(CH₂D)(CD₃), —CD(CHD₂)(CHD₂), —CD(CHD₂)(CD₃), —CD(CD₃)₂, and—C(CD₃)₃, but embodiments are not limited thereto.

In some embodiments, in Formula 1, the deuterium-containing substituentmay be selected from

-D, —CD₃, —CD(CH₃)₂, —CD(CD₃)₂, and —C(CD₃)₃, but embodiments are notlimited thereto.

In Formula 1, a moiety represented by

(wherein * and *′ each indicate a binding site to Ir in Formula 1) mayinclude at least one deuterium.

Whether the moiety represented by

includes a deuterium or not may be identified by analyzing the ¹H NMRspectrum or molecular weight measured using a molecular weightmeasurement device such as a matrix-assisted laserdesorption-ionization-time-of-flight mass spectrometer.

For example, a compound (hereinafter referred to as a “first referencecompound”) having a backbone that is identical to the backbone of theorganometallic compound represented by Formula 1 but including nodeuterium atom may be prepared. The ¹H NMR spectra of the firstreference compound and the organometallic compound represented byFormula 1 may be obtained. Then, by comparing integral values of signalsat a certain ppm in the obtained spectra of the first reference compoundand the organometallic compound with each other, the number of hydrogenatoms at certain positions (i.e., hydrogen atoms bound to certaincarbons) in the organometallic compound represented by Formula 1 thatare substituted with deuterium may be determined.

Alternatively, existence of a compound (hereinafter referred to as a“second reference compound”) having a backbone that is identical to thebackbone of the organometallic compound represented by Formula 1,wherein all hydrogen atoms are substituted with deuterium may beassumed. By comparing the calculated molecular weight of the secondreference compound with the molecular weight of the organometalliccompound represented by Formula 1, the number of hydrogen atoms in theorganometallic compound represented by Formula 1 that are substitutedwith deuterium may be determined.

In some embodiments, the organometallic compound represented by Formula1 may have a deuteration degree, which is determined by Equation 1, of50% or more, but embodiments are not limited thereto:Deuteration degree (%)=n _(D1)/(n _(H1) +n _(D1))×100  Equation 1

wherein in Equation 1,

n_(H1) indicates the total number of hydrogens included in thedeuterium-containing substituents of the organometallic compoundrepresented by Formula 1;

n_(D1) indicates the total number of deuteriums included in thedeuterium-containing substituents of the organometallic compoundrepresented by Formula 1.

In some embodiments, a deuteration degree determined by Equation 1 ofthe organometallic compound represented by Formula 1 may be 70% or more,but embodiments are not limited thereto.

In some embodiments, a deuteration degree determined by Equation 1 ofthe organometallic compound represented by Formula 1 may be 90% or more,but embodiments are not limited thereto.

In Formula 1, n11 indicates the number of ligands represented by

and n11 may be selected from 1, 2, and 3. When n11 is 2 or more, ligandsrepresented by

may be identical to or different from each other.

In some embodiments, in Formula 1, n11 may be 3, but embodiments are notlimited thereto.

In Formula 1, L₁₁ may be selected from a monodentate ligand and abidentate ligand.

In some embodiments, in Formula 1, L₁₁ may be selected from amonodentate ligand, and L₁₁ may be selected from I⁻, Br⁻, Cl⁻, asulfide, a nitrate, an azide, a hydroxide, a cyanate, an isocyanate, athiocyanate, water, acetonitrile, a pyridine, ammonia, carbon monoxide,P(Ph)₃, P(Ph)₂CH₃, PPh(CH₃)₂, and P(CH₃)₃, but embodiments are notlimited thereto.

In some embodiments, in Formula 1, L₁₁ may be selected from bidentateligands, and L₁₁ may be selected from an oxalate, an acetylacetonate, apicolinic acid, a 1,2-bis(diphenylphosphino)ethane, a1,1-bis(diphenylphosphino)methane, a glycinate, an ethylenediamine, andone of Formulae 4-1 to 4-4, but embodiments are not limited thereto:

wherein in Formulae 4-1 to 4-4,

X₄₁ may be selected from CR₄₁ and a nitrogen atom (N); X₄₂ may beselected from CR₄₂ and N;

Y₄₁ and Y₄₂ may be each independently selected from a carbon (C) atomand N;

A₄₁ to A₄₃ may be each independently selected from a C₃-C₁₀ cycloalkane,a C₁-C₁₀ heterocycloalkene, a C₃-C₁₀ cycloalkene, a C₁-C₁₀heterocycloalkene, a C₆-C₁₀ arene, a C₁-C₁₀ heteroarene, a non-aromaticcondensed polycycle, and a non-aromatic condensed heteropolycycle;

R₄₁ to R₄₄ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and —Si(Q₄₁)(Q₄₂)(Q₄₃); wherein

b43 and b44 may be each independently an integer selected from 1 to 5;

Q₄₁ to Q₄₃ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group;and

* and *′ each independently indicate a binding site to Ir in Formula 1.

In some embodiments, in Formula 1, L₁₁ may be represented by one ofFormulae 4-1 to 4-4;

A₄₁ to A₄₃ may be each independently selected from a benzene, anaphthalene, a fluorene, a spiro-fluorene, an indene, a furan, athiophene, a carbazole, a benzofuran, a benzothiophene, a dibenzofuran,a dibenzothiophene, a pyrrole, an imidazole, a pyrazole, a thiazole, anisothiazole, an oxazole, an isoxazole, a triazole, a pyridine, apyrazine, a pyrimidine, a quinoline, an isoquinoline, a benzoquinoline,a quinoxaline, a quinazoline, a naphthyridine, a benzoimidazole, abenzoxazole, an isobenzoxazole, an oxadiazole, and a triazine;

R₄₁ to R₄₄ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₆₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

—Si(Q₄₁)(Q₄₂)(Q₄₃); wherein

b43 and b44 may be each independently an integer selected from 1 to 3;

Q₄₁ to Q₄₃ may be each independently selected from a C₁-C₁₀ alkyl group,a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 1, L₁₁ may be represented by one ofFormulae 4-1 to 4-4;

A₄₁ may be selected from a pyridine, an imidazole, a pyrazole, atriazole, and a tetrazole,

A₄₂ may be selected from a benzene, a pyridine, a pyrazine, apyrimidine, and a triazine,

A₄₃ may be selected from a benzene and a pyridine;

R₄₁ to R₄₄ may be each independently selected from a hydrogen, —F, acyano group, a nitro group, a methyl group, an ethyl group, a propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decanyl group, an iso-decanyl group, a sec-decanyl group, atert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a pentoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a methyl group, an ethyl group, a propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decanyl group, an iso-decanylgroup, a sec-decanyl group, a tert-decanyl group, a methoxy group, anethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,each substituted with at least one selected from —F, a cyano group, anda nitro group;

b43 and b44 may be each independently an integer selected from 1 to 3,but embodiments are not limited thereto.

In some embodiments, L₁₁ in Formula 1 may be represented by one ofFormulae 5-1 to 5-119, but embodiments are not limited thereto:

wherein in Formulae 5-1 to 5-119,

R₅₁ to R₅₃ may be each independently selected from a hydrogen, —F, acyano group, a nitro group, a methyl group, an ethyl group, a propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decanyl group, an iso-decanyl group, a sec-decanyl group, atert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a pentoxy group, a phenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a methyl group, an ethyl group, a propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decanyl group, an iso-decanylgroup, a sec-decanyl group, a tert-decanyl group, a methoxy group, anethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenylgroup, a naphthyl group, a pyridinyl group, a pyrimidinyl group, atriazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,each substituted with at least one selected from —F, a cyano group, anda nitro group;

b51 and b54 may be each independently selected from 1 and 2;

b53 and b55 may be each independently an integer selected from 1 to 3;

b52 may be an integer selected from 1 to 4; and

* and *′ may be each independently a binding site to a neighboring atom.

In Formula 1, m11 indicates the number of groups L₁₁, and m11 may beselected from 0, 1, 2, 3, and 4. When m11 is 2 or more, a plurality ofgroups L₁₁ may be identical to or different from each other. In someembodiments, in Formula 1, m11 may be 0, but embodiments are not limitedthereto.

In Formula 1, n11 and m11 may be properly controlled based on thecoordination number of Ir. For example, when n11 is 3, m11 may be 0. Insome embodiments, if L₁₁ is a bidentate ligand, when n11 is 2, m11 maybe 1. In some embodiments, if L₁₁ is a bidentate ligand, when n11 is 1,m11 may be 2.

In some embodiments, the organometallic compound may be represented byFormula 1-1, but embodiments are not limited thereto:

wherein in Formula 1-1,

descriptions of R₁₁, R₁₃, R₁₅ to R₂₀, L₁₁, n11, and m11 are the same asin Formula 1.

In some embodiments, the organometallic compound may be represented byFormula 1-11, but embodiments are not limited thereto:

wherein in Formula 1-11,

descriptions of R₁₁, R₁₃, R₁₅, R₁₇, R₁₉, R₂₀, L₁₁, n11, and m11 are thesame as in Formula 1.

In some embodiments, the organometallic compound may be represented byone of Formulae 1-21 and 1-22, but embodiments are not limited thereto:

wherein in Formulae 1-21 and 1-22,

descriptions of R₁₃, R₁₇, R₁₉, R₂₀, L₁₁, n11, and m11 are the same as inFormula 1; and

R_(x1) to R_(x3) are each independently understood by referring to thedescriptions of the deuterium-containing substituent in Formula 1.

In some embodiments, the organometallic compound may be selected fromCompounds 1 to 24, but embodiments are not limited thereto:

A maximum emission wavelength of the organometallic compound may be 440nm to 465 nm or less. When the maximum emission wavelength thereof is440 nm to 465 nm or less, the organic light-emitting device may providea deep blue emission color.

The organometallic compound represented by Formula 1 may provide a deepblue emission color by including “a cyano group” at a “specificposition”.

As shown in Formula 1′, when a cyano group is at a para position withrespect to a Ir—C binding site, the organometallic compound of Formula 1may have a deep highest occupied molecular orbital (HOMO) energy level.Accordingly, the organometallic compound of Formula 1 may have a hightriplet energy level due to an increased band gap, and thus provide adeep blue emission color.

The organometallic compound represented by Formula 1 essentiallyincludes “a deuterium”, thereby having improved thermal stability.Particularly, a carbon-deuterium single bond has a stronger bondstrength and shorter bond length than a carbon-hydrogen single bond.Thus, an organometallic compound including a deuterium has high thermalstability, compared to the thermal stability of an organometalliccompound that does not include a deuterium. Therefore, when storingand/or operating an organic light-emitting device including theorganometallic compound represented by Formula 1, dissociation of theorganometallic compound into radicals due to heat and/or an electricfield occurs substantially slowly. Thus, the organic light-emittingdevice including the organometallic compound may have improved lifespancharacteristics.

The HOMO energy level, lowest unoccupied molecular orbital (LUMO) energylevel, T1 energy level, and maximum emission wavelength of someorganometallic compounds represented by Formula 1 were evaluated byusing Gaussian 09 that performs molecular structure optimizationsaccording to density functional theory (DFT) based on B3LYP. The resultsthereof are shown in Table 1.

TABLE 1 Compound No. HOMO (eV) LUMO (eV) T1 (eV) λ_(max) (nm) 6 −5.28−1.18 2.78 446 7 −5.28 −1.17 2.78 445 16  −5.18 −1.05 2.79 444 A −4.90−0.89 2.71 458 B −5.18 −1.50 2.48 499 C −5.14 −1.47 2.39 520 D −5.28−1.18 2.78 446 E −5.28 −1.17 2.78 445 F −5.18 −1.05 2.79 444

An organometallic compound that does not include deuterium may besynthesized by a method similar to the method of preparation of theorganometallic compound of Formula 1. In this regard, according toanother aspect of the present disclosure, a composition containing anorganometallic compound represented by Formula 2 (hereinafter referredto as a “second organometallic compound”) as well as the organometalliccompound represented by Formula 1 (hereinafter referred to as a “firstorganometallic compound”) may be provided:

wherein in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be each independentlyselected from a hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a carbonyl group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₂-C₁₀ alkynyl group, and a substituted orunsubstituted C₁-C₁₀ alkoxy group.

In some embodiments, in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, and a substituted or unsubstituted C₁-C₁₀ alkylgroup, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a cyano group,and a C₁-C₁₀ alkyl group; and

a C₁-C₁₀ alkyl group substituted with at least one selected from —F,—Cl, —Br, —I, and a cyano group; but embodiments are not limitedthereto.

In some embodiments, in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a cyano group,and a C₁-C₁₀ alkyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a cyano group,a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, anda tert-pentyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁, R₂₂, and R₂₄ to R₂₈ may be eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a cyano group,a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, and atert-butyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁, R₂₅, and R₂₇ may be eachindependently selected from

a hydrogen, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, and a tert-butyl group, butembodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁ or R₂₅ may be selected from ahydrogen, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, and a tert-butyl group, butembodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁ and R₂₅ may be each independentlyselected from a hydrogen, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, acarbonyl group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₁₀ linear alkyl group, a substitutedor unsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, and a substituted or unsubstituted C₁-C₁₀ alkoxygroup.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, acarbonyl group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,and a substituted or unsubstituted C₁-C₁₀ linear alkyl group, butembodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,—F, —Cl, —Br, —I, a cyano group, a C₁-C₁₀ linear alkyl group; and

a C₁-C₁₀ linear alkyl group substituted with at least one selected from—F, —Cl, —Br, —I, and a cyano group; but embodiments are not limitedthereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, and a C₁-C₁₀ linear alkylgroup, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an n-butyl group, and an n-pentyl group, butembodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, and an n-butyl group, but embodiments are notlimited thereto.

In some embodiments, in Formula 2, R₂₃ may be selected from a hydrogen,a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, and anethyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₁ and R₂₂, R₂₂ and R₂₃, R₂₃ andR₂₄, or R₂₄ and R₂₅ may be optionally bound to each other so as to forma condensed ring, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₅ and R₂₆ may be optionally boundto each other via a single bond, but embodiments are not limitedthereto.

In Formula 2, R₂₉ and R₃₀ may be each independently selected from ahydrogen and a C₁-C₁₀ alkyl group.

In some embodiments, in Formula 2, R₂₉ and R₃₀ may be each independentlyselected from

a hydrogen; and a methyl group, an ethyl group, an n-propyl group, aniso-propyl group, an n-butyl group, a sec-butyl group, an iso-butylgroup, and a tert-butyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 2, R₂₉ and R₃₀ may be a hydrogen, butembodiments are not limited thereto.

In Formula 2, R₂₁ to R₃₀ may be each independently a substituentcontaining no deuterium.

In the present specification, a non-deuterium containing substituentrefers to a substituent in which any hydrogen atom therein issubstituted with a deuterium atom.

In Formula 2, a moiety represented by

(wherein * and *′ each indicate a binding site to Ir in Formula 2) maynot include a deuterium atom.

In some embodiments, provided is a composition containing anorganometallic compound that includes the first organometallic compoundand the second organometallic compound. The organometallic compound mayhave a deuteration degree of 50% or more, as determined by Equation 2,but embodiments are not limited thereto:Deuteration degree (%)=n _(D2)/(n _(H2) +n _(D2))×100  Equation 2

wherein in Equation 2,

n_(H2) represents a sum of a total number of hydrogens in thedeuterium-containing substituents of the first organometallic compoundand a total number of hydrogens in substituents of the secondorganometallic compound that are equivalent (correspond) to thedeuterium-containing substituents of the first organometallic compound;and

n_(D2) represents a total number of deuteriums in thedeuterium-containing substituents of the first organometallic compound.

If a substituent in the dashed region in Compound 1′ is adeuterium-containing substituent, the “substituents that are equivalentto the deuterium-containing substituents” used herein may include asubstituent in the dashed region in Compound 1″. That is, substituentsbound at the same carbon location in two compounds that are the sameexcept for having or not having an isotope thereof are defined as“equivalent” substituents.

For example, when the first organometallic compound includes twodeuterium-containing substituents, n_(D2) indicates the number of alldeuterium atoms included in the two deuterium-containing substituents ofthe first organometallic compound. In addition, n_(H2) indicates thetotal number of hydrogens included in the two deuterium-containingsubstituents of the first organometallic compound and the total numberof hydrogens included in substituents of the second organometalliccompound corresponding to the two deuterium-containing substituents ofthe first organometallic compound.

In some embodiments, the deuteration degree may be 70% or more, 90% ormore, 95% or more, 96% or more, 97% or more, 98% or more, or 99% ormore, but embodiments are not limited thereto.

A method of synthesizing the organometallic compound represented byFormula 1 may be apparent to one of ordinary skill in the art byreferring to Synthesis Examples used herein. The composition containingthe organometallic compound may be obtained as a result of imperfectdeuteration taken place during the synthesis of the organometalliccompound represented by Formula 1, not by further addition at least onesecond organometallic compound.

Therefore, the organometallic compound represented by Formula 1 or thecomposition containing an organometallic compound may be used in anorganic layer of an organic light-emitting device, for example, as adopant in an emission layer of the organic layer. According to anotheraspect, there is provided an organic light-emitting device thatincludes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and theorganometallic compound represented by Formula 1 or the compositioncontaining the organometallic compound.

The organic light-emitting device may provide a high efficiency, longlifespan, and high color coordination by including an organic layer thatcontains the organometallic compound represented by Formula 1 or thecomposition containing the organometallic compound.

The organometallic compound represented by Formula 1 or the compositioncontaining an organometallic compound may be used in a pair ofelectrodes in an organic light-emitting device. In some embodiments, theorganometallic compound represented by Formula 1 or the compositioncontaining the organometallic compound may be included in the emissionlayer. In this regard, the organometallic compound may serve as adopant, and the emission layer may further include a host. The emissionlayer may emit red light, green light, or blue light.

As used herein, “(for example, the organic layer) including anorganometallic compound” means that “(the organic layer) including anorganometallic compound of Formula 1 above, or at least two differentorganometallic compounds of Formula 1 above”.

For example, the organic layer may include only Compound 1 as theorganometallic compound. In this regard, Compound 1 may be included inthe emission layer of the organic light-emitting device. Alternatively,the organic layer may include Compound 1 and Compound 2 as theorganometallic compounds. In this regard, Compound 1 and Compound 2 maybe included in the same layer (for example, both Compound 1 and Compound2 may be included in the emission layer).

The first electrode may be anode, which is a hole injection electrode,and the second electrode may be a cathode, which is an electroninjection electrode. Alternatively, the first electrode may be acathode, which is an electron injection electrode, and the secondelectrode may be an anode, which is a hole injection electrode.

For example,

the first electrode may be an anode,

the second electrode may be a cathode, and

the organic layer may include:

i) a hole-transport region disposed between the first electrode and theemission layer, wherein the hole-transport region includes at least oneselected from a hole injection layer, a hole-transport layer, and anelectron blocking layer; and

ii) an electron-transport region disposed between the emission layer andthe second electrode, wherein the electron-transport region includes atleast one selected from a hole blocking layer, an electron transportlayer, and an electron injection layer.

As used herein, the term the “organic layer” refers to a single and/or aplurality of layers disposed between the first electrode and the secondelectrode in an organic light-emitting device. The “organic layer” mayinclude not only organic compounds but also organometallic complexesincluding metals.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an exemplary embodiment. Hereinafter, a structure and amethod of manufacturing the organic light-emitting device 10 accordingto an exemplary embodiment will be described with reference to FIG. 1.The organic light-emitting device 10 includes a first electrode 11, anorganic layer 15, and a second electrode 19, which are sequentiallylayered in the stated order.

A substrate may be additionally disposed under the first electrode 11 oron the second electrode 19. The substrate may be a conventionalsubstrate that is used in an organic light-emitting device, such asglass substrate or a transparent plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellency.

The first electrode 11 may be formed by vacuum-depositing or sputteringa material for forming the first electrode 11 on the substrate. Thefirst electrode 11 may be an anode. The material for the first electrode11 may be selected from materials with a high work function for an easyhole injection. The first electrode 11 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. The materialfor the first electrode 11 may be selected from indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO).Alternatively, a metal such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag).

The first electrode 11 may have a single layer structure or amulti-layer structure including a plurality of layers. For example, thefirst electrode 11 may have a triple-layer structure of ITO/Ag/ITO, butembodiments are not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, hole transport layer, electron blocking layer, andbuffer layer.

The hole transport region may only include a hole injection layer or ahole transport layer. Alternatively, the hole transport region mayinclude a structure in which a hole injection layer/a hole transportlayer or a hole injection layer/a hole transport layer/an electronblocking layer are sequentially layered on the first electrode 11.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 11 by using variousmethods such as vacuum-deposition, spin coating, casting, andLangmuir-Blodgett (LB) methods.

When a hole injection layer is formed by vacuum-deposition, for example,the vacuum-deposition may be performed at a deposition temperature in arange of about 100° C. to about 500° C., at a vacuum degree in a rangeof about 10⁻⁸ to about 10⁻³ torr, and at a deposition rate in a range ofabout 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, though theconditions may vary depending on a compound that is used as a holeinjection material and a structure and thermal properties of a desiredhole injection layer, but embodiments are not limited thereto.

When a hole injection layer is formed by spin coating, the spin coatingmay be performed at a coating rate in a range of about 2000 revolutionsper minute (rpm) to about 5,000 rpm, and at a temperature in a range ofabout 80° C. to 200° C. for removing a solvent after the spin coating,though the conditions may vary depending on a compound that is used as ahole injection material and a structure and thermal properties of adesired HIL, but embodiments are not limited thereto.

The conditions for forming a hole transport layer and an electronblocking layer may be inferred based on the conditions for forming thehole injection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201, and a compound represented by Formula 202:

wherein in Formula 201, Ar₁₀₁ and Ar₁₀₂ may be each independentlyselected from

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylene groupand a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.

In Formula 201, xa may be each independently an integer selected from 0to 5, and xb may be an integer selected from 0, 1, and 2. In someembodiments, xa may be 1 and xb may be 0, but embodiments are notlimited thereto.

In Formula 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ maybe each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group (such as, a methyl group, an ethyl group,a propyl group, a butyl group, a pentyl group, or a hexyl group), and aC₁-C₁₀ alkoxy group (such as, a methoxy group, an ethoxy group, apropoxy group, a butoxy group, or a pentoxy group);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but embodiments are notlimited thereto.

In Formula 201, R₁₀₉ may be selected from

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, and a pyridinyl group.

In some embodiments, the compound represented by Formula 201 may berepresented by Formula 201A, but embodiments are not limited thereto:

Descriptions of R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A are the sameas described above.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20, butembodiments are not limited thereto:

The thickness of the hole transport region may be in a range of about100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about1,000 Å. When the hole transport region includes a hole injection layerand a hole transport layer, the thickness of the hole injection layermay be in a range of about 100 Å to about 10,000 Å, and for example,about 100 Å to about 1,000 Å, and the thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, and for example,about 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer, and the hole transport layer arewithin these ranges, excellent hole transport characteristics may beobtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thementioned materials above, a charge-generating material to improveconductive properties. The charge-generating material may behomogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. For example, non-limiting examples of the p-dopant are aquinone derivative, such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; and acompound containing a cyano group, such as Compound HT-D1 or HT-D2, butembodiments are not limited thereto:

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer toimprove the efficiency of an organic light-emitting device.

An emission layer may be formed on the hole transport region by usingvarious methods, such as vacuum-deposition, spin coating, casting, or anLB method. When the emission layer is formed by vacuum-deposition orspin coating, vacuum-deposition and coating conditions for the emissionlayer may be generally similar to the conditions for forming a holeinjection layer, though the conditions may vary depending on thecompound used.

The emission layer may include a host and a dopant.

The host may include at least one selected from CBP, CDBP, TCP, and mCP:

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer.Alternatively, the emission layer may have a structure in which the redemission layer, the green emission layer, and/or the blue emission layerare layered to emit white light or other various embodiments arepossible.

The emission layer may include the organometallic compound representedby Formula 1 as a dopant.

When the emission layer includes the host and the dopant, the amount ofthe dopant may be selected from a range of about 0.01 part by weight toabout 20 parts by weight based on about 100 parts by weight of the host,but embodiments are not limited thereto.

The thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be formed on the emission layer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer, but embodiments not limited thereto.

For example, the electron transport region may have a structure of ahole blocking layer/an electron transport layer/an electron injectionlayer or an electron transport layer/an electron injection layer, butembodiments are not limited thereto. The electron transport layer mayhave a single layer structure or a multi-layer structure including twoor more different materials.

The conditions for forming a hole blocking layer, an electron transportlayer, and an electron injection layer may be inferred based on theconditions for forming the hole injection layer.

When the electron transport region includes an hole blocking layer, thehole blocking layer may, for example, include at least one of BCP andBphen, but embodiments are not limited thereto:

The thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. When thethickness of the hole blocking layer is within this range, excellenthole blocking characteristics may be obtained without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, BPhen, Alq3, BAlq, TAZ, and NTAZ:

Alternatively, the electron transport layer may include at least oneselected from Compounds ET1 to ET19, but embodiments are not limitedthereto:

The thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within this range,excellent electron transport characteristics may be obtained without asubstantial increase in driving voltage.

The electron transport layer may further include a metal-containingmaterial in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 19.

The electron injection layer may include at least one selected from LiF,NaCl, CsF, Li₂O, and BaO.

The thickness of the electron injection layer may be in a range of about1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within this range,excellent electron injection characteristics may be obtained without asubstantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for the second electrode 19may be a material having a relatively low work function, such as ametal, an alloy, an electrically conductive compound, and a mixturethereof. Detailed examples of the material for forming the secondelectrode 19 are lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag). Alternatively, ITO or IZO may be used to forma transmissive second electrode 19 to manufacture a top emissionlight-emitting device, and such a variation may be possible.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but embodiments are not limited thereto.

A C₁-C₁₀ alkyl group as used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 10 carbon atoms.Detailed examples thereof include a methyl group, an ethyl group, apropyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an iso-amyl group, and a hexyl group.

A C₁-C₁₀ linear alkyl group as used herein refers to a linear aliphatichydrogen carbon monovalent group having 1 to 10 carbon atoms. A C₁-C₁₀linear alkyl group is a C₁-C₁₀ alkyl group, excluding a branched alkylgroup, such as iso-propyl group. Examples of the C₁-C₁₀ linear alkylgroup include a n-propyl group and an n-butyl group.

A C₁-C₁₀ alkoxy group as used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is a C₁-C₁₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₁₀ alkenyl group as used herein refers to a group formed bysubstituting at least one carbon double bond in the middle or at theterminal of the C₂-C₁₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group.

A C₂-C₁₀ alkynyl group as used herein refers to a group formed bysubstituting at least one carbon triple bond in the middle or at theterminal of the C₂-C₁₀ alkyl group. Detailed examples thereof are anethenyl group and a propenyl group.

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalenthydrocarbon monocyclic group having 3 to 10 carbon atoms. Detailedexamples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as the C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentmonocyclic group having at least one heteroatom selected from N, O, P,and S as a ring-forming atom and 1 to 10 carbon atoms. Detailed examplesthereof are a tetrahydrofuranyl group and a tetrahydrothiophenyl group.A C₁-C₁₀ heterocycloalkylene group as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof, and which is not aromatic. Detailed examplesthereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group as used hereinrefers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group that has at least one heteroatom selected from N, O,Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at leastone double bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as theC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving a carbocyclic aromatic system that has at least one heteroatomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. A C₁-C₆₀ heteroarylene group as used herein refers to a divalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to60 carbon atoms. Detailed examples of the C₁-C₆₀ heteroaryl group are apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylenegroup each include two or more rings, the rings may be fused to eachother.

A C₆-C₆₀ aryloxy group as used herein indicates —OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as used hereinindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group (e.g., a grouphaving 8 to 60 carbon atoms) as used herein refers to a monovalent groupthat has two or more rings condensed to each other, has carbon atomsonly as a ring-forming atom, and which is non-aromatic in the entiremolecular structure. A detailed example of the monovalent non-aromaticcondensed polycyclic group is a fluorenyl group. A divalent non-aromaticcondensed polycyclic group as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group (e.g., agroup having 1 to 60 carbon atoms) as used herein refers to a monovalentgroup that has two or more rings condensed to each other, hasheteroatoms as a ring-forming atom selected from N, O, P, and S inaddition to C, and which is non-aromatic in the entire molecularstructure. A detailed example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. A divalent non-aromaticcondensed heteropolycyclic group as used herein refers to a divalentgroup having the same structure as the monovalent non-aromatic condensedheteropolycyclic group.

In the present specification, at least one substituent of thesubstituted C₁-C₁₀ alkyl group, substituted C₁-C₁₀ linear alkyl group,substituted C₂-C₁₀ alkenyl group, substituted C₂-C₁₀ alkynyl group, andsubstituted C₁-C₁₀ alkoxy group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₂-C₁₀ alkenyl group, a C₂-C₁₀ alkynyl group, and aC₁-C₁₀ alkoxy group; and

a C₁-C₁₀ alkyl group, a C₂-C₁₀ alkenyl group, a C₂-C₁₀ alkynyl group,and a C₁-C₁₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, and a phosphoric acid group or a saltthereof.

Hereinafter, an organic light-emitting device according to an exemplaryembodiment will be described in detail with reference to SynthesisExamples and Examples; however, the present inventive concept is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that the amount of B used wasidentical to the amount of A used based on molar equivalence.

EXAMPLE Synthesis Example 1: Synthesis of Compound 6

1) Synthesis of Intermediate 6-1

50 millimoles (mmol) (11.42 grams (g)) of1-(2,6-diisopropylphenyl)-1H-imidazole and 2.5 mmol (5 percent by weight(wt %)) of Pd/C were mixed with 200 milliliters (ml) of D₂O and 40 ml ofMeOD. The mixture was stirred in a sealed tube at 180° C. under ahydrogen atmosphere for 24 hours. The resulting mixture was cooled,diluted in an ethyl acetate solution, and filtered. An organic layer wasextracted with ethyl acetate. The obtained organic layer was washed withwater three times and dried with magnesium sulfate (MgSO₄). The crudeproduct was obtained therefrom by removing a solvent under reducedpressure. The crude product was purified by silica gel columnchromatography (wherein, dichloromethane and hexane were used as aneluent), thereby obtaining 9.57 g of Intermediate 6-1 (yield: 90%).

MALDI-TOF (m/z): 239.33 [M]⁺

2) Synthesis of Intermediate 6-2

9.57 g of Intermediate 6-1, 90 ml of tetrahydrofuran (THF), and 17.7 mlof n-BuLi (44 mmol, 2.5 M solution in n-hexane) were added to a reactionvessel under a nitrogen atmosphere, at −78° C. The mixture was stirredfor about an hour. Thereafter, 40 mmol (6.39 g) of Br₂ was added theretoat −78° C. About 30 minutes after, a cooling bath was removed, and theresulting mixture was stirred at room temperature for about 6 hours.Once the reaction was complete, an organic layer was quenched with waterand extracted with dichloromethane. The obtained organic layer waswashed with water three times, and dried with MgSO₄. The crude productwas obtained therefrom by removing a solvent under reduced pressure. Thecrude product was purified by silica gel column chromatography (wherein,dichloromethane and hexane were used as an eluent), thereby obtaining9.64 g of Intermediate 6-2 (yield: 73%).

MALDI-TOF (m/z): 318.23 [M]⁺

3) Synthesis of Intermediate 6-3

9.64 g (30 mmol) of Intermediate 6-2, 7.43 g (45 mmol)3-cyano-4-fluorophenyl)boronic acid, 1.04 g (0.9 mmol) oftetrakis-(triphenylphosphine) palladium(0), 12.42 g (90 mmol) ofpotassium carbonate, 90 mL of toluene, and 60 mL of water were added to90 mL of THF and the mixture was refluxed for 72 hours. The result wascooled, quenched with water, and the organic layer was extracted withethyl acetate. The obtained organic layer was washed with water threetimes, and dried with MgSO₄. The crude product was obtained therefrom byremoving a solvent under reduced pressure. The crude product waspurified by silica gel column chromatography (wherein, dichloromethaneand hexane were used as an eluent), thereby obtaining 8.64 g ofIntermediate 6-3 (yield: 86%).

MALDI-TOF (m/z): 340.18 [M]⁺

4) Synthesis of Compound 6

A mixture of 2.5 g (5 mmol) of Ir(acac)₃, 8.64 g (25 mmol) ofIntermediate 6-3, and 150 mL of glycerol in a 500 mL reaction vessel wasrefluxed under a nitrogen atmosphere for 12 hours. Once the reaction wascomplete, the resulting mixture was cooled to room temperature. 300 mLof distilled water was added to the reaction vessel, thereby forming asolid. The formed solid was filtered and washed with 1 L of distilledwater. The solid was dried, and was purified with silica gel columnchromatography (wherein, dichloromethane and hexane were used as aneluent), thereby obtaining Compound 6 (yield: 24%).

MALDI-TOF (m/z): 1206.83 [M]⁺

Synthesis Example 2: Synthesis of Compound 7

1) Synthesis of Intermediate 7-1

7.88 g of Intermediate 7-1 (yield: 88%) was synthesized in the samemanner as Intermediate 6-1, except that1-(2,6-dimethylphenyl)-1H-imidazole was used instead of1-(2,6-diisopropylphenyl)-1H-imidazole.

MALDI-TOF (m/z): 179.10 [M]⁺

2) Synthesis of Intermediate 7-2

8.51 g of Intermediate 7-2 (yield: 75%) was synthesized in the samemanner as Intermediate 6-2, except that Intermediate 7-1 was usedinstead of Intermediate 6-1.

MALDI-TOF (m/z): 257.99 [M]⁺

3) Synthesis of Intermediate 7-3

7.86 g of Intermediate 7-3 (yield: 85%) was synthesized in the samemanner as Intermediate 6-3, except that Intermediate 7-2 was usedinstead of Intermediate 6-2.

MALDI-TOF (m/z): 280.20 [M]⁺

4) Synthesis of Compound 7

1.31 g of Compound 7 (yield: 18%) was synthesized in the same manner asCompound 6, except that Intermediate 7-3 was used instead ofIntermediate 6-3.

MALDI-TOF (m/z): 1034.58 [M]⁺

Synthesis Example 3: Synthesis of Compound 16

1) Synthesis of Intermediate 16-1

13.52 g of Intermediate 16-1 (yield: 90%) was synthesized in the samemanner as Intermediate 6-1, except that 5-amino-2-methylbenzonitrile wasused instead of 1-(2,6-diisopropylphenyl)-1H-imidazole.

MALDI-TOF (m/z): 135.21 [M]⁺

2) Synthesis of Intermediate 16-2

13.52 g (100 mmol) of Intermediate 16-1 was added to 100 ml ofacetonitrile, 6.90 g (100 mmol) of sodium nitrite dissolved in 50 ml ofwater at −25° C. was slowly added thereto, and subsequently, 34.5 ml(300 mmol) 48% HBr was slowly added thereto. The mixture was stirred forabout an hour at −25° C. Thereafter, 150 mmol (21.55 g) of CuBr wasadded thereto. Then, a cooling bath was removed, and the resultingmixture was stirred at room temperature for about 20 hours. The reactionwas quenched by adding water, and the pH thereof was adjusted to 10 byadding a saturated sodium carbonate solution. An organic layer wasextracted with dichloromethane. The obtained organic layer was washedwith water three times, and dried with MgSO₄. The crude product wasobtained therefrom by removing a solvent under reduced pressure. Thecrude product was purified by silica gel column chromatography (wherein,dichloromethane and hexane were used as an eluent), thereby obtaining9.95 g of Intermediate 16-2 (yield: 56%).

MALDI-TOF (m/z): 199.16 [M]⁺

3) Synthesis of Intermediate 16-3

9.95 g (50 mmol) of Intermediate 16-3, 9.81 g (100 mmol) of potassiumacetate, and 15.47 g (60 mmol) of4,4,4′,4′,5,5,5′,5-octamethyl-2,2′-bi-1,3,2-dioxaborolane were added to100 ml of N,N-dimethylformamide (DMF), and the mixture was stirred atroom temperature. 2.56 g (3.5 mmol) of[1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (II)(PdCl₂(dppf)) was added thereto and the resulting mixture was refluxedat 80° C. for 12 hours. The obtained mixture was cooled, diluted byusing ethyl acetate, and was filtered through celite. The obtainedorganic layer was washed with water three times, and dried by usingMgSO₄. The crude product was obtained therefrom by removing a solventunder reduced pressure. The crude product was purified by silica gelcolumn chromatography (wherein, dichloromethane and hexane were used asan eluent), thereby obtaining 8.72 g of Intermediate 16-3 (yield: 71%).

MALDI-TOF (m/z): 245.59 [M]⁺

4) Synthesis of Intermediate 16-4

7.86 g of Intermediate 16-4 (yield: 85%) was synthesized in the samemanner as Intermediate 6-3, except that Intermediate 16-2 was usedinstead of Intermediate 16-3.

MALDI-TOF (m/z): 260.38 [M]⁺

5) Synthesis of Compound 16

2.76 g of Compound 16 (yield: 29%) was synthesized in the same manner asCompound 6, except that Intermediate 16-4 was used instead ofIntermediate 6-3.

MALDI-TOF (m/z): 1261.63 [M]⁺

Evaluation Example 1: Evaluation on HOMO, LUMO, and Triplet (T1) EnergyLevels

HOMO, LUMO, and T1 energy levels of Compounds 6, 7, 16, and D to F wereevaluated according to the method in Table 2. Results thereof are shownin Table 3.

TABLE 2 HOMO energy level A potential (Volts, V) - current (Amperes, A)graph of each compound was evaluation method obtained by using cyclicvoltammetry (CV) (electrolyte: 0.1M Bu₄NClO₄/ solvent: CH₂Cl₂/electrode:3 electrode system (working electrode: GC, reference electrode: Ag/AgCl,auxiliary electrode: Pt)). Then, from reduction onset of the graph, aHOMO energy level of a compound was calculated. LUMO energy level Eachcompound was diluted at a concentration of 1 × 10⁻⁵M in CHCl₃, and a UVevaluation method absorption spectrum thereof was measured at roomtemperature by using a Shimadzu UV-350 spectrometer. Then a LUMO energylevel thereof was calculated by using an optical band gap (Eg) from anedge of the absorption spectrum. T1 energy level A mixture (eachcompound was dissolved in an amount of 1 milligram (mg) in 3 evaluationmethod cubic centimeters (cc) of toluene) of toluene and each compoundwas loaded into a quartz cell. Then, the resultant quartz cell wasloaded into liquid nitrogen (77 Kelvin (K)), a photoluminescencespectrum thereof was measured by using a device for measuringphotoluminescence, and the obtained spectrum was compared with aphotoluminescence spectrum measured at room temperature, and peaksobserved only at a low temperature were analyzed to calculate T1 energylevels.

TABLE 3 Compound No. HOMO (eV) LUMO (eV) T1 (eV)  6 −5.36 −2.41 2.69  7−5.28 −2.53 2.69 16 −5.27 −2.49 2.72 D −5.42 −2.75 2.68 E −5.35 −2.602.68 F −5.21 −2.27 2.71

From Table 3, it is found that Compounds 6, 7, and 16 have electriccharacteristics that are suitable as a material for forming an organiclight-emitting device.

Evaluation Example 2: Thermal Characteristics Evaluation

Thermal analysis (N₂ atmosphere, temperature range: room temperature to600° C. (10° C./min), and Pan Type: Pt Pan in disposable Al Pan) wasperformed on Compounds 6, 7, 16, and D to F by using thermo gravimetricanalysis (TGA). The results thereof are shown in Table 4. In addition,TGA results of Compounds 6 and 7 are shown in graphs in FIGS. 2A and 2Bfor illustrative purposes:

TABLE 4 Compound No. Td (1%, ° C.) 6 402 7 461 16  383 D 398 E 445 F 368

Referring to Table 4, Compound 6 has higher Td than Compound D, Compound7 has higher Td than Compound E, and Compound 16 has higher Td thanCompound F. From Table 4, it was found that the organometallic compoundrepresented by Formula 1 has excellent thermal stability due tosubstituting hydrogen atoms with deuterium atoms.

Evaluation Example 3: Emission Spectrum Evaluation

The Photoluminescence (PL) spectrum of Compounds 6, 7, 16, and A to Fwere measured to evaluate emission characteristics of each compound.Compound 6 was dissolved at a concentration of 10 millimolar (mM) inCHCl₃. Then an ISC PC1 spectrofluorometer, in which a Xenon lamp wasmounted, was used to measure a PL spectrum of Compound 1 at roomtemperature. The same process was repeated for Compounds 7, 16, and D toF.

The maximum wavelength of PL spectra of Compounds 7, 16, and D to F areshown in Table 5. In addition, PL spectra of Compounds 6 and 7 are shownin FIGS. 3A and 3B, respectively.

TABLE 5 Compound No. λ_(max) (nm) 6 461 7 461 16  456 D 463 E 462 F 457

Referring to Table 5, it was found that compounds, in which a cyanogroup is positioned at a para position with respect to the Ir-carbonbond (that is, Compounds 6, 7, 16, and D to F), have a maximum emissionwavelength of 465 nanometers (nm) or less. On the other hand, compounds,in which a cyano group is not positioned at a para position with respectto Ir-carbon bond (that is, Compounds A to C), have a maximum emissionwavelength of greater than 465 nm. From the results above, it was foundthat in order to provide a deep blue emission color, it is desired thata cyano group is substituted at a para position with respect to theIr-carbon binding site. From Table 5, it is found that the Compounds 6,7, and 16 have excellent emission characteristics.

Example 1

As a first electrode (an anode), a glass substrate having an ITOelectrode deposited thereon at a thickness of 1,500 Å was washed withdistilled water in the presence of ultrasound waves. Once the washingwith distilled water was complete, ultrasound wave washing was performedon the substrate by using a solvent such as isopropyl alcohol, acetone,or methanol. Then, the substrate was dried, transferred to a plasmawasher, washed for 5 minutes using oxygen plasma, and mounted in avacuum depositor.

Compound HT3 was vacuum-deposited on the ITO electrode of the glasssubstrate to form a first hole injection layer having a thickness ofabout 3,500 Å, Compound HT-D1 was vacuum-deposited on the first holeinjection layer to form a second hole injection layer having a thicknessof about 300 Å, and TAPC was vacuum-deposited on the second holeinjection layer to form an electron blocking layer having a thickness ofabout 100 Å, thereby forming a hole transport region.

mCP (host) and Compound 1 (dopant, 7 wt %) were co-deposited on the holetransport region to form an emission layer having a thickness of about300 Å.

Compound ET3 was vacuum-deposited on the emission layer to form anelectron transport layer having a thickness of about 250 Å, ET-D1 (Liq)was vacuum-deposited on the electron transport layer to form an electroninjection layer having a thickness of about 5 Å, and an Al secondelectrode (a cathode) was formed on the electron injection layer to havea thickness of about 1,000 Å, thereby completing the manufacture of anorganic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 7 was used instead of Compound 6 as adopant in the formation of the emission layer.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 16 was used instead of Compound 6 asa dopant in the formation of the emission layer.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound D was used instead of Compound 6 as adopant in the formation of the emission layer.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound E was used instead of Compound 6 as adopant in the formation of the emission layer.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound F was used instead of Compound 6 as adopant in the formation of the emission layer.

Evaluation Example 4: Evaluation of Characteristics of OrganicLight-Emitting Device

The EL spectrum, current density change according to voltage, luminancechange according to voltage, conversion efficiency, lifespan, and CIEcolor-coordinate of each organic light-emitting device manufactured inExample 1 and Comparative Example 1 were measured. A detailedmeasurement method is as described below, and the results thereof areshown in Table 6. In addition, the current density changes according tovoltage, EL spectra, conversion efficiency changes according toluminance, and lifespan results of the organic light-emitting devicemanufactured in Example 1 and Comparative Example 1 are shown in FIGS. 4to 7, respectively.

(1) Measurement of EL Spectra

EL spectra of the prepared organic light-emitting devices at a luminanceof about 500 candelas per square meter (cd/m²) were measured by using aluminance meter (Minolta Cs-1000A).

(2) Measurement of Current Density Changes According to Voltage

Current values of the prepared organic light-emitting devices weremeasured by measuring values of current in a unit device thereof using acurrent voltmeter (Keithley 2400) while increasing the applied voltagefrom about 0 Volts (V) to about 10 V. The result was obtained bydividing a current value by an area.

(3) Measurement of Luminance Changes According to Voltage

Luminance values of the prepared organic light-emitting devices weremeasured by using a luminance meter (Minolta Cs-1000A) while increasingthe applied voltage from about 0 V to about 10 V.

(4) Measurement of Conversion Efficiencies

The luminance values measured from (3) and current density valuesmeasured from (2), and applied voltages were used in calculating currentefficiencies (cd/A) under a condition of an identical current density(10 milliamperes per square centimeter (mA/cm²)). Then, the currentefficiencies were divided by a y value of the CIE color-coordinatemeasured in (6) in order to calculate conversion efficiencies.

(5) Measurement of Lifespan

T₉₅, which indicates a period of time taken for the luminance to reach95% with respect to 100% of the luminance measured in (3), and T₅₀,which indicates a period of time taken for the luminance to reach 50%with respect to 100% of the luminance measured in (3), were calculated.

(6) Measurement of CIE Color-Coordinate

Color-coordinates of the prepared organic light-emitting devices at aluminance of about 500 cd/m² were measured by using a luminance meter(Minolta Cs-1000A).

TABLE 6 Emission Current Color- layer density Luminance EfficiencyConversion EL T95 T50 coordinate Host Dopant (mA/cm²) (cd/m²) (cd/A)efficiency (nm) (Hour) (Hour) (x, y) Example 1 mCP 6 10 500 37.21 143.20460 8.88 360.00 (0.17, 0.26) Example 2 mCP 7 10 500 35.93 135.30 46014.44 400.00 (0.17, 0.27) Example 3 mCP 16 10 500 31.54 150.20 456 4.66160.00 (0.16, 0.21) Comparative mCP D 10 500 36.47 137.80 460 4.49130.00 (0.17, 0.26) Example 1 Comparative mCP E 10 500 35.57 125.50 4602.42 110.00 (0.17, 0.26) Example 2 Comparative mCP F 10 500 31.18 140.0456 2.64 140.00 (0.17, 0.23) Example 3

Referring to Table 6, it is confirmed that the organic light-emittingdevices prepared in Examples 1 to 3 have improved characteristics,compared to the organic light-emitting devices prepared in ComparativeExamples 1 to 3.

As described above, according to the one or more of the above exemplaryembodiments, the organometallic compound has excellent opticalcharacteristics, electrical characteristics, and thermal stability.Accordingly, an organic light-emitting device using the organometalliccompound may have improved efficiency, lifespan, and color puritycharacteristics.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each exemplaryembodiment should typically be considered as available for other similarfeatures or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described withreference to the figures, it will be understood by those of ordinaryskill in the art that various changes in form and details may be madetherein without departing from the spirit and scope of the presentinventive concept as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein in Formula 1, R₁₁, R₁₂, and R₁₄ to R₁₈ are each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxygroup, a cyano group, a nitro group, a carbonyl group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group,a substituted or unsubstituted C₂-C₁₀ alkynyl group, and a substitutedor unsubstituted C₁-C₁₀ alkoxy group; R₁₃ is selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxy group, a cyano group, a nitrogroup, a carbonyl group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₁₀ linear alkyl group, asubstituted or unsubstituted C₂-C₁₀ alkenyl group, a substituted orunsubstituted C₂-C₁₀ alkynyl group, and a substituted or unsubstitutedC₁-C₁₀ alkoxy group; R₁₉ and R₂₀ are each independently selected from ahydrogen, a deuterium, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkyl groupsubstituted with a deuterium; R₁₁ and R₁₂, R₁₂ and R₁₃, R₁₃ and R₁₄, orR₁₄ and R₁₅ are optionally linked to each other to form a condensedring; at least one selected from R₁₁ to R₂₀ is a C₁-C₁₀ alkyl groupsubstituted with a deuterium, provided that when R₁₃ is selected, R₁₃ isa C₁-C₁₀ linear alkyl group substituted with a deuterium; n11 isselected from 1, 2, and 3; L₁₁ is selected from a monodentate ligand anda bidentate ligand; and m11 is selected from 0, 1, 2, 3, and
 4. 2. Theorganometallic compound of claim 1, wherein R₁₁, R₁₂, and R₁₄ to R₁₈ areeach independently selected from a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxy group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, and a substituted orunsubstituted C₁-C₁₀ alkyl group.
 3. The organometallic compound ofclaim 1, wherein R₁₁, R₁₂, and R₁₄ to R₁₈ are each independentlyselected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group,a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, anda tert-pentyl group; and a methyl group, an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, a sec-butyl group, aniso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentylgroup, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group,a 1,2-dimethylpropyl group, and a tert-pentyl group, each substitutedwith a deuterium.
 4. The organometallic compound of claim 1, wherein atleast one of R₁₁ is R₁₅ are independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, and a tert-butyl group; and amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butylgroup, each substituted with a deuterium.
 5. The organometallic compoundof claim 1, wherein R₁₃ is selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxy group, a cyano group, a nitro group, a carbonylgroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, and asubstituted or unsubstituted C₁-C₁₀ linear alkyl group.
 6. Theorganometallic compound of claim 1, wherein R₁₃ is selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group,an ethyl group, an n-propyl group, an n-butyl group, and an n-pentylgroup; and a methyl group, an ethyl group, an n-propyl group, an n-butylgroup, and an n-pentyl group, each substituted with a deuterium.
 7. Theorganometallic compound of claim 1, wherein R₁₉ is a deuterium, and R₂₀is a hydrogen; R₁₉ is a hydrogen, and R₂₀ is a deuterium; or R₁₉ and R₂₀are both a deuterium.
 8. The organometallic compound of claim 1, whereinat least one of R₁₁ and R₁₅ is a C₁-C₁₀ alkyl group substituted with adeuterium.
 9. The organometallic compound of claim 1, wherein the atleast one selected from R₁₁ to R₂₀ is selected from a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutylgroup, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentylgroup, each substituted with a deuterium, wherein selection of R₁₃ issubject to limitations of claim
 1. 10. The organometallic compound ofclaim 1, wherein L₁₁ is a bidentate ligand.
 11. The organometalliccompound of claim 1, wherein L₁₁ is represented by one of Formulae 4-1to 4-4:

wherein in Formulae 4-1 to 4-4, X₄₁ is selected from CR₄₁ and N; X₄₂ isselected from CR₄₂ and N; Y₄₁ and Y₄₂ are each independently selectedfrom C and N; A₄₁ to A₄₃ are each independently selected from a C₃-C₁₀cycloalkane, a C₁-C₁₀ heterocycloalkane, a C₃-C₁₀ cycloalkene, a C₁-C₁₀heterocycloalkene, a C₆-C₁₀ arene, a C₁-C₁₀ heteroarene, a non-aromaticcondensed polycycle, and a non-aromatic condensed heteropolycycle; R₄₁to R₄₄ are each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxy group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and —Si(Q₄₁)(Q₄₂)(Q₄₃); b43 and b44 are each independently an integerselected from 1 to 5; Q₄₁ to Q₄₃ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group; and * and *′ each independentlyindicate a binding site to Ir in Formula
 1. 12. The organometalliccompound of claim 1, represented by Formula 1-1:

wherein in Formula 1-1, R₁₁, R₁₃, R₁₅ to R₂₀, L₁₁, n11, and m11 are thesame as defined in Formula
 1. 13. The organometallic compound of claim1, represented by one of Formulae 1-21 and 1-22:

wherein in Formulae 1-21 and 1-22, R₁₃, R₁₇, R₁₉, R₂₀, L₁₁, n11, and m11are the same as defined in Formula 1; and at least one of R_(x1) toR_(x3) is a C₁-C₁₀ alkyl group substituted with a deuterium.
 14. Theorganometallic compound of claim 1, selected from Compounds 1 to 24:


15. The organometallic compound of claim 1, wherein each of R₁₁, R₁₅,and R₁₇ is a C₁-C₁₀ alkyl group substituted with a deuterium.
 16. Acomposition comprising an organometallic compound, comprising: a firstorganometallic compound represented by Formula 1 and a secondorganometallic compound represented by Formula 2:

wherein in Formulae 1 and 2, R₁₁, R₁₂, and R₁₄ to R₁₈ are eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxy group, a cyano group, a nitro group, a carbonyl group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀alkenyl group, a substituted or unsubstituted C₂-C₁₀ alkynyl group, anda substituted or unsubstituted C₁-C₁₀ alkoxy group; R₁₃ is selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy group, a cyanogroup, a nitro group, a carbonyl group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀linear alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group,a substituted or unsubstituted C₂-C₁₀ alkynyl group, and a substitutedor unsubstituted C₁-C₁₀ alkoxy group; R₁₉ and R₂₀ are each independentlyselected from a hydrogen, a deuterium, a C₁-C₁₀ alkyl group, and aC₁-C₁₀ alkyl group substituted with a deuterium; at least one of R₁₁ toR₂₀ comprises a deuterium; R₂₁, R₂₂, and R₂₄ to R₂₈ are eachindependently selected from a hydrogen, —F, —Cl, —Br, —I, a hydroxygroup, a cyano group, a nitro group, a carbonyl group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group,a substituted or unsubstituted C₂-C₁₀ alkynyl group, and a substitutedor unsubstituted C₁-C₁₀ alkoxy group; R₂₃ is selected from a hydrogen,—F, —Cl, —Br, —I, a hydroxy group, a cyano group, a nitro group, acarbonyl group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₁₀ linear alkyl group, a substitutedor unsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, and a substituted or unsubstituted C₁-C₁₀ alkoxygroup; R₂₉ and R₃₀ are each independently selected from a hydrogen and aC₁-C₁₀ alkyl group; R₂₁ to R₃₀ are each a substituent comprising nodeuterium; n11 and n21 are each independently selected from 1, 2, and 3;L₁₁ and L₂₁ are each independently selected from a monodentate ligandand a bidentate ligand; and m11 and m21 are each independently selectedfrom 0, 1, 2, 3, and
 4. 17. The composition of claim 16, wherein thefirst organometallic compound has a deuteration degree of 50% orgreater, as determined by Equation 2:Deuteration degree (%)=n _(D2)/(n _(H2) +n _(D2))×100  Equation 2wherein in Equation 2, n_(H2) indicates the total number of hydrogenscomprised in the at least one of R₁₁ to R₂₀ comprising deuterium of thefirst organometallic compound and the total number of hydrogenscomprised in substituents of the second organometallic compound locatedat identical positions and corresponding to the at least one of R₁₁ toR₂₀ comprising deuterium of the first organometallic compound; andn_(D2) indicates the total number of deuteriums comprised in the atleast one of R₁₁ to R₂₀ of the first organometallic compound.
 18. Anorganic light-emitting device comprising: a first electrode; a secondelectrode; and an organic layer disposed between the first electrode andthe second electrode, wherein the organic layer comprises an emissionlayer and the organometallic compound of claim
 1. 19. The organiclight-emitting device of claim 18, wherein the emission layer comprisesthe organometallic compound; wherein the emission layer furthercomprises a host; and wherein the organometallic compound comprised inthe emission layer is a dopant.